Penicillin acylase-catalyzed peptide synthesis in aqueous medium: A chemo-enzymatic route to stereoisomerically pure diketopiperazines

Andrei Y. Khimiuk; Alexei V. Korennykh; Luuk M. Van Langen; Fred Van Rantwijk; Roger A. Sheldon; Vytas K. Švedas

doi:10.1016/j.tetasy.2003.08.011

Penicillin acylase-catalyzed peptide synthesis in aqueous medium: A chemo-enzymatic route to stereoisomerically pure diketopiperazines

Andrei Y. Khimiuk
, Alexei V. Korennykh
, Luuk M. Van Langen
, Fred Van Rantwijk
, Roger A. Sheldon
, Vytas K. Švedas

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

A range of non-natural dipeptides of the general formula D-(-)-phenylglycyl-L-X, where X is a natural α-amino acid, have been prepared by penicillin acylase-catalyzed synthesis in aqueous medium from D-(-)-phenylglycine amide and the corresponding amino acids. The conversion of the dipeptides to the corresponding dipeptide esters, followed by their subsequent spontaneous cyclization afforded the corresponding stereoisomerically pure diketopiperazines.

Original language	English (US)
Pages (from-to)	3123-3128
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	14
Issue number	20
DOIs	https://doi.org/10.1016/j.tetasy.2003.08.011
State	Published - Oct 17 2003
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2003.08.011

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title = "Penicillin acylase-catalyzed peptide synthesis in aqueous medium: A chemo-enzymatic route to stereoisomerically pure diketopiperazines",

abstract = "A range of non-natural dipeptides of the general formula D-(-)-phenylglycyl-L-X, where X is a natural α-amino acid, have been prepared by penicillin acylase-catalyzed synthesis in aqueous medium from D-(-)-phenylglycine amide and the corresponding amino acids. The conversion of the dipeptides to the corresponding dipeptide esters, followed by their subsequent spontaneous cyclization afforded the corresponding stereoisomerically pure diketopiperazines.",

author = "Khimiuk, \{Andrei Y.\} and Korennykh, \{Alexei V.\} and \{Van Langen\}, \{Luuk M.\} and \{Van Rantwijk\}, Fred and Sheldon, \{Roger A.\} and {\v S}vedas, \{Vytas K.\}",

note = "Funding Information: Financial support by the Russian Foundation for Basic Research (grant 03-04-48472), INTAS (grant 2001-0673), DSM Life Science products and the Netherlands Ministry of Economic Affairs is gratefully acknowledged. Thanks are due to Messrs. A. van Estrik and A. Sinnema for the NMR analyses and to Mrs. A. Knol for the MS measurements.",

year = "2003",

month = oct,

day = "17",

doi = "10.1016/j.tetasy.2003.08.011",

language = "English (US)",

volume = "14",

pages = "3123--3128",

journal = "Tetrahedron Asymmetry",

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publisher = "Elsevier Ltd",

number = "20",

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TY - JOUR

T1 - Penicillin acylase-catalyzed peptide synthesis in aqueous medium

T2 - A chemo-enzymatic route to stereoisomerically pure diketopiperazines

AU - Khimiuk, Andrei Y.

AU - Korennykh, Alexei V.

AU - Van Langen, Luuk M.

AU - Van Rantwijk, Fred

AU - Sheldon, Roger A.

AU - Švedas, Vytas K.

N1 - Funding Information: Financial support by the Russian Foundation for Basic Research (grant 03-04-48472), INTAS (grant 2001-0673), DSM Life Science products and the Netherlands Ministry of Economic Affairs is gratefully acknowledged. Thanks are due to Messrs. A. van Estrik and A. Sinnema for the NMR analyses and to Mrs. A. Knol for the MS measurements.

PY - 2003/10/17

Y1 - 2003/10/17

N2 - A range of non-natural dipeptides of the general formula D-(-)-phenylglycyl-L-X, where X is a natural α-amino acid, have been prepared by penicillin acylase-catalyzed synthesis in aqueous medium from D-(-)-phenylglycine amide and the corresponding amino acids. The conversion of the dipeptides to the corresponding dipeptide esters, followed by their subsequent spontaneous cyclization afforded the corresponding stereoisomerically pure diketopiperazines.

AB - A range of non-natural dipeptides of the general formula D-(-)-phenylglycyl-L-X, where X is a natural α-amino acid, have been prepared by penicillin acylase-catalyzed synthesis in aqueous medium from D-(-)-phenylglycine amide and the corresponding amino acids. The conversion of the dipeptides to the corresponding dipeptide esters, followed by their subsequent spontaneous cyclization afforded the corresponding stereoisomerically pure diketopiperazines.

UR - https://www.scopus.com/pages/publications/1642339679

UR - https://www.scopus.com/pages/publications/1642339679#tab=citedBy

U2 - 10.1016/j.tetasy.2003.08.011

DO - 10.1016/j.tetasy.2003.08.011

M3 - Article

AN - SCOPUS:1642339679

SN - 0957-4166

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SP - 3123

EP - 3128

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 20

ER -

Penicillin acylase-catalyzed peptide synthesis in aqueous medium: A chemo-enzymatic route to stereoisomerically pure diketopiperazines

Abstract

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